Stereoselective synthesis of an eleganine A core
Gints Smits1, Ronalds Zemribo1
1Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga, LV-1006, Latvia. gintssmits@osi.lv.
Abstract:
A synthetic approach towards the core of a structurally unique cytotoxic indole alkaloid eleganine A has been accomplished for the first time. The synthesis features a stereoselective Ireland-Claisen rearrangement as the key step, enabling the installation of 2 stereogenic centers and a stereodefined double bond in a single step. Furthermore, a SnCl4 promoted acylation of the indole C-2 position allows the coupling of a highly functionalized 4-ethylidene proline fragment with the indole part.
Related Concept Videos
E2 Reaction: Stereochemistry and Regiochemistry
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major...
E1 Reaction: Stereochemistry and Regiochemistry
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Regioselective Formation of Enolates
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Alkylation of β-Diester Enolates: Malonic Ester Synthesis


